Acetic Acid → 2-Chloro-9H-fluoren-9-one hydrazone

HRID 1073328Notes

Reaction equation

HRID 1073328 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=O)[C:4]=2[CH:3]=1.O.[NH2:17][NH2:18].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[N:17][NH2:18])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 183542-Chloro-9H-fluoren-9-oneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 536740962-Chloro-9H-fluoren-9-one hydrazoneYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro 9-fluorenone (18) (5 g, 23.3 mmoL), hydrazine monohydrate (6 mL, 120 mmoL, 5.2 eq) and acetic acid (1 mL) in ethanol (150 mL ) was refluxed for 2.5 h. The mixture was then evaporated to dryness to provide 5.3 g (100%) of product which was used without further purification: mp 139°-143° C..

Workup

  1. temperaturewas refluxed for 2.5 h
  2. customThe mixture was then evaporated to dryness

Sources & evidence

ORD record
ord-7c3541d3688d477789bb658bd4de9314
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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